The association between preoperative cognitive status and surgical outcomes is a critical, yet scarcely explored area of research. Linking intraoperative data with postoperative outcomes is a promising and low-cost way of evaluating long-term impacts of surgical interventions. In this study, we evaluated how preoperative cognitive status as measured by the clock drawing test contributed to predicting length of hospital stay, hospital charges, average pain experienced during follow-up, and 1-year mortality over and above intraoperative variables, demographics, preoperative physical status and comorbidities. We expanded our analysis to 6 specific surgical groups where sufficient data was available for cross-validation. The clock drawing images were represented by 10 constructional features discovered by a semi-supervised deep learning algorithm, previously validated to differentiate between dementia and non-dementia patients. Different machine learning models were trained to classify postoperative outcomes in hold-out test sets. The models were compared to their relative performance, time complexity, and interpretability. Shapley Additive Explanations (SHAP) analysis was used to find the most predictive features for classifying different outcomes in different surgical contexts. Relative classification performances achieved by different feature sets showed that the perioperative cognitive dataset which included clock drawing features in addition to intraoperative variables, demographics, and comorbidities served as the best dataset for 12 of 18 possible surgery-outcome combinations...